CA3185469A1 - Heteroaryl substituted spiropiperidinyl derivatives and pharmaceutical uses thereof - Google Patents
Heteroaryl substituted spiropiperidinyl derivatives and pharmaceutical uses thereofInfo
- Publication number
- CA3185469A1 CA3185469A1 CA3185469A CA3185469A CA3185469A1 CA 3185469 A1 CA3185469 A1 CA 3185469A1 CA 3185469 A CA3185469 A CA 3185469A CA 3185469 A CA3185469 A CA 3185469A CA 3185469 A1 CA3185469 A1 CA 3185469A1
- Authority
- CA
- Canada
- Prior art keywords
- 6alkyl
- diazaspiro
- undecan
- pyrimidin
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/537—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines spiro-condensed or forming part of bridged ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20191191.4 | 2020-08-14 | ||
| EP20191191 | 2020-08-14 | ||
| PCT/IB2021/057427 WO2022034529A1 (en) | 2020-08-14 | 2021-08-12 | Heteroaryl substituted spiropiperidinyl derivatives and pharmaceutical uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3185469A1 true CA3185469A1 (en) | 2022-02-17 |
Family
ID=72088005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3185469A Pending CA3185469A1 (en) | 2020-08-14 | 2021-08-12 | Heteroaryl substituted spiropiperidinyl derivatives and pharmaceutical uses thereof |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US11708366B2 (es) |
| EP (1) | EP4196478A1 (es) |
| JP (1) | JP2023537357A (es) |
| KR (1) | KR20230051227A (es) |
| CN (1) | CN116157404A (es) |
| AR (1) | AR123241A1 (es) |
| AU (2) | AU2021325431B2 (es) |
| BR (1) | BR112023002031A2 (es) |
| CA (1) | CA3185469A1 (es) |
| CL (1) | CL2023000418A1 (es) |
| CO (1) | CO2023002940A2 (es) |
| CR (1) | CR20230125A (es) |
| DO (1) | DOP2023000028A (es) |
| EC (1) | ECSP23017158A (es) |
| IL (1) | IL299091A (es) |
| MX (1) | MX2023001725A (es) |
| PE (1) | PE20230855A1 (es) |
| TW (1) | TW202220990A (es) |
| UY (1) | UY39377A (es) |
| WO (1) | WO2022034529A1 (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11932630B2 (en) | 2021-04-16 | 2024-03-19 | Novartis Ag | Heteroaryl aminopropanol derivatives |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3998834A (en) | 1975-03-14 | 1976-12-21 | Janssen Pharmaceutica N.V. | N-(4-piperidinyl)-n-phenylamides and -carbamates |
| GB9913083D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| US20040110826A1 (en) | 2001-09-28 | 2004-06-10 | Noriaki Uesaka | Receptor Antagonists |
| PE20050130A1 (es) | 2002-08-09 | 2005-03-29 | Novartis Ag | Compuestos organicos |
| NL2000323C2 (nl) | 2005-12-20 | 2007-11-20 | Pfizer Ltd | Pyrimidine-derivaten. |
| NZ583642A (en) | 2007-09-04 | 2012-03-30 | Biolipox Ab | Bis-aromatic compounds useful in the treatment of inflammation |
| WO2011110824A1 (en) * | 2010-03-12 | 2011-09-15 | Biolipox Ab | Bis aromatic compounds for use as ltc4 synthase inhibitors |
| WO2011076747A1 (en) | 2009-12-21 | 2011-06-30 | Novartis Ag | Diaza-spiro[5.5]undecanes as orexin receptor antagonists |
| CA2803056C (en) | 2010-06-23 | 2017-05-16 | Hanmi Science Co., Ltd. | Fused pyrimidine derivatives for inhibition of tyrosine kinase activity |
| CN103096716B (zh) | 2010-08-10 | 2016-03-02 | 西建阿维拉米斯研究公司 | Btk抑制剂的苯磺酸盐 |
| US20120101110A1 (en) | 2010-10-26 | 2012-04-26 | Sangamesh Badiger | Diaza-spiro[5.5]undecanes |
| EA023876B1 (ru) | 2011-03-14 | 2016-07-29 | Бёрингер Ингельхайм Интернациональ Гмбх | Бензодиоксановые ингибиторы продуцирования лейкотриена |
| CN106831732B (zh) | 2011-06-10 | 2019-12-24 | 默克专利有限公司 | 生产具有btk抑制活性的嘧啶和吡啶化合物的组合物和方法 |
| US9139567B2 (en) | 2011-07-19 | 2015-09-22 | Boehringer Ingelheim International Gmbh | Arylpyrazole ethers as inhibitors of leukotriene A4 hydrolase |
| UA111756C2 (uk) | 2011-11-03 | 2016-06-10 | Ф. Хоффманн-Ля Рош Аг | Сполуки гетероарилпіридону та азапіридону як інгібітори тирозинкінази брутона |
| NZ626750A (en) | 2011-11-29 | 2015-08-28 | Ono Pharmaceutical Co | Purinone derivative hydrochloride |
| EP2822941B1 (en) | 2012-03-06 | 2017-05-10 | Boehringer Ingelheim International GmbH | Benzodioxanes in combination with statins for inhibiting leukotriene production |
| AR091315A1 (es) | 2012-03-06 | 2015-01-28 | Boehringer Ingelheim Int | Inhibidores de benzodioxano de la produccion de leucotrieno |
| US9353087B2 (en) | 2012-06-08 | 2016-05-31 | Biogen Ma Inc. | Inhibitors of Bruton's tyrosine kinase |
| TW201416354A (zh) | 2012-07-17 | 2014-05-01 | Boehringer Ingelheim Int | 白三烯生成抑制劑 |
| PT3181567T (pt) | 2012-09-10 | 2019-06-24 | Principia Biopharma Inc | Compostos de pirazolopirimidina como inibidores de cinase |
| WO2014117920A1 (en) | 2013-02-04 | 2014-08-07 | Merck Patent Gmbh | Spiro-quinazolinone derivatives useful for the treatment of neurological diseases and conditions |
| JO3377B1 (ar) | 2013-03-11 | 2019-03-13 | Takeda Pharmaceuticals Co | مشتقات بيريدينيل وبيريدينيل مندمج |
| RU2686101C2 (ru) | 2013-03-12 | 2019-04-24 | Селтакссис, Инк. | Способы ингибирования лейкотриен- а4-гидролазы |
| AU2014239567B2 (en) | 2013-03-14 | 2017-12-14 | Celtaxsys, Inc. | Inhibitors of leukotriene A4 hydrolase |
| BR112015022226A2 (pt) | 2013-03-14 | 2017-07-18 | Celtaxsys Inc | inibidores de leucotrieno a4 hidrolase |
| EP2968265A4 (en) | 2013-03-14 | 2016-12-28 | Celtaxsys Inc | INHIBITORS OF THE LEUKOTRIEN A4 HYDROLASE |
| ES2619125T3 (es) | 2013-04-25 | 2017-06-23 | Beigene, Ltd. | Compuestos heterocíclicos fusionados como inhibidores de proteína cinasa |
| WO2015009609A1 (en) | 2013-07-15 | 2015-01-22 | Boehringer Ingelheim International Gmbh | Inhibitors of leukotriene production |
| EP3022194B1 (en) | 2013-07-15 | 2017-05-17 | Boehringer Ingelheim International GmbH | Inhibitors of leukotriene production |
| US9512084B2 (en) | 2013-11-29 | 2016-12-06 | Novartis Ag | Amino pyrimidine derivatives |
| US10328080B2 (en) | 2013-12-05 | 2019-06-25 | Acerta Pharma, B.V. | Therapeutic combination of PI3K inhibitor and a BTK inhibitor |
| AP2016009301A0 (en) | 2013-12-20 | 2016-06-30 | Novartis Ag | Heteroaryl butanoic acid derivatives as lta4h inhibitors |
| WO2015110923A2 (en) | 2014-01-21 | 2015-07-30 | Acerta Pharma B.V. | Methods of treating chronic lymphocytic leukemia and small lymphocytic leukemia usng a btk inhibitor |
| KR102030305B1 (ko) | 2014-10-24 | 2019-10-08 | 브리스톨-마이어스 스큅 컴퍼니 | 키나제 억제제로서 유용한 인돌 카르복스아미드 화합물 |
| RU2719446C2 (ru) | 2014-11-03 | 2020-04-17 | Айомет Фарма Лтд | Фармацевтическое соединение |
| US10022359B2 (en) * | 2014-11-21 | 2018-07-17 | Esteve Pharmaceuticals, S.A. | 1,9-diazaspiro undecane compounds having multimodal activity against pain |
| US20180015088A1 (en) | 2014-12-24 | 2018-01-18 | Principia Biopharma Inc. | Site specific dosing of a btk inhibitor |
| GB201507753D0 (en) * | 2015-05-06 | 2015-06-17 | Biolipox Ab | New compounds and uses |
| EA039006B1 (ru) | 2015-06-03 | 2021-11-19 | Принсипиа Биофарма Инк. | Ингибиторы тирозинкиназы |
| US20180282310A1 (en) | 2015-06-10 | 2018-10-04 | Biogen Ma Inc. | Forms and compositions of biaryl inhibitors of bruton's tyrosine kinase |
| US10533011B2 (en) | 2015-10-09 | 2020-01-14 | ACEA Therapeutics, Inc. | Pharmaceutical salts, physical forms, and compositions of pyrrolopyrimidine kinase inhibitors, and methods of making same |
| JP6913100B2 (ja) | 2015-11-04 | 2021-08-04 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Ｂｔｋ阻害活性を有するピリミジン及びピリジン化合物を用いた癌の治療方法 |
| US9630968B1 (en) | 2015-12-23 | 2017-04-25 | Arqule, Inc. | Tetrahydropyranyl amino-pyrrolopyrimidinone and methods of use thereof |
| PL3372607T3 (pl) | 2016-01-05 | 2021-09-20 | Jiangsu Hengrui Medicine Co. Ltd. | Postać krystaliczna inhibitora kinazy btk i sposób jego otrzymywania |
| AU2017290354C1 (en) | 2016-06-29 | 2023-07-06 | Principia Biopharma Inc. | Modified release formulations of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| WO2018119263A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds derivatives as pd-l1 internalization inducers |
-
2021
- 2021-08-12 BR BR112023002031A patent/BR112023002031A2/pt unknown
- 2021-08-12 EP EP21755587.9A patent/EP4196478A1/en active Pending
- 2021-08-12 AU AU2021325431A patent/AU2021325431B2/en active Active
- 2021-08-12 US US17/400,458 patent/US11708366B2/en active Active
- 2021-08-12 IL IL299091A patent/IL299091A/en unknown
- 2021-08-12 TW TW110129822A patent/TW202220990A/zh unknown
- 2021-08-12 WO PCT/IB2021/057427 patent/WO2022034529A1/en active Application Filing
- 2021-08-12 PE PE2023000248A patent/PE20230855A1/es unknown
- 2021-08-12 CN CN202180060257.4A patent/CN116157404A/zh active Pending
- 2021-08-12 KR KR1020237008311A patent/KR20230051227A/ko active Search and Examination
- 2021-08-12 JP JP2023507892A patent/JP2023537357A/ja active Pending
- 2021-08-12 AR ARP210102276A patent/AR123241A1/es unknown
- 2021-08-12 MX MX2023001725A patent/MX2023001725A/es unknown
- 2021-08-12 UY UY0001039377A patent/UY39377A/es unknown
- 2021-08-12 CA CA3185469A patent/CA3185469A1/en active Pending
- 2021-08-12 CR CR20230125A patent/CR20230125A/es unknown
-
2023
- 2023-02-10 DO DO2023000028A patent/DOP2023000028A/es unknown
- 2023-02-10 CL CL2023000418A patent/CL2023000418A1/es unknown
- 2023-03-10 CO CONC2023/0002940A patent/CO2023002940A2/es unknown
- 2023-03-10 EC ECSENADI202317158A patent/ECSP23017158A/es unknown
- 2023-05-18 US US18/319,585 patent/US20240043425A1/en active Pending
-
2024
- 2024-01-04 AU AU2024200054A patent/AU2024200054A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ECSP23017158A (es) | 2023-04-28 |
| CN116157404A (zh) | 2023-05-23 |
| AU2021325431B2 (en) | 2024-01-18 |
| CL2023000418A1 (es) | 2023-09-29 |
| US11708366B2 (en) | 2023-07-25 |
| KR20230051227A (ko) | 2023-04-17 |
| US20240043425A1 (en) | 2024-02-08 |
| IL299091A (en) | 2023-02-01 |
| CO2023002940A2 (es) | 2023-03-17 |
| WO2022034529A1 (en) | 2022-02-17 |
| CR20230125A (es) | 2023-05-11 |
| PE20230855A1 (es) | 2023-05-29 |
| MX2023001725A (es) | 2023-02-22 |
| US20220048909A1 (en) | 2022-02-17 |
| BR112023002031A2 (pt) | 2023-03-07 |
| UY39377A (es) | 2022-03-31 |
| TW202220990A (zh) | 2022-06-01 |
| AR123241A1 (es) | 2022-11-09 |
| AU2024200054A1 (en) | 2024-01-25 |
| JP2023537357A (ja) | 2023-08-31 |
| EP4196478A1 (en) | 2023-06-21 |
| AU2021325431A1 (en) | 2023-01-19 |
| DOP2023000028A (es) | 2023-03-15 |
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